Propargyl alcohol → HCID 178522867, compound

HRID 2289965Notes

Reaction equation

HRID 2289965 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]([C:12]2[CH:13]=[N:14][C:15]3[C:20]([C:21]=2[OH:22])=[CH:19][CH:18]=[C:17](I)[CH:16]=3)=[O:11])=[CH:4][CH:3]=1.[CH2:24]([OH:27])[C:25]#[CH:26]>C(NCC)C.[Cu](I)I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]([C:12]2[CH:13]=[N:14][C:15]3[C:20]([C:21]=2[OH:22])=[CH:19][CH:18]=[C:17]([C:26]#[C:25][CH2:24][OH:27])[CH:16]=3)=[O:11])=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 7859Propargyl alcoholHCID 178522889HCID 178522889, compound

Product 1

HCID 178522867HCID 178522867, compound

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8021DiethylamineSolvent

Procedure

To a mixture of the title compound of Example 39 (0.439 g), copper iodide (0.010 g) and dichlorobis(triphenylphosphine)palladium (II) (0.035 g) in 15 mL diethylamine is added propargyl alcohol (0.058 mL). The reaction is allowed to stir overnight. The solvents are evaporated and the residue is chromatographed on silica, eluting with 3% MeOH/CH2Cl2 to yield 0.271 g of the desired product as a tan solid.

Workup

  1. customThe solvents are evaporated
  2. customthe residue is chromatographed on silica
  3. washeluting with 3% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-d0991543aae94a9499ff4b6f6b4cf1ce
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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